Process for the preparation of rice seed for sowing

ABSTRACT

A method for preparing rice seed for sowing whereby the seed is pregerminated and thereafter treated with a plant growth regulator and, optionally, a phytoprotection product such as an insecticide.

CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application is a divisional of prior copending U.S. patentapplication Ser. No. 08/916,266, filed Aug. 22, 1997, incorporated byreference herein in its entirety and relied upon. Application Ser. No.08/916,266 is a continuation-in-part of application Ser. No. 08/656,966,filed Jun. 6, 1996, now abandoned, which claims the priority of U.S.Provisional Patent Application No. 60/000,024, filed Jun. 8, 1995;application Ser. No. 08/916,266 is also a continuation-in-part ofapplication Ser. No. 08/873,468, filed Jun. 12, 1997, now abandoned,which claims the priority of U.S. Provisional Patent Application No.60/019,667 filed Jun. 12, 1996.

[0002] The present invention relates to a process for the preparation ofrice seed for sowing.

[0003] Rice crops are attacked by a number of pests. A useful method ofprotecting rice and rice seed and rice crop is to apply one or morephytoprotection products to the seed by different methods such ascoating, soaking or dipping. Although it is well-known that dry orungerminated seeds can be coated with a phytoprotection product andsubsequently sown, a common practice is to pregerminate rice seed bysoaking the seed in water containing one or more phytoprotectionproducts followed by a period in which the soaked, treated seed isallowed to drain and produce a radicle. (The period during which theseed is soaked, drained and during which a radicle is produced is calledthe pregermination period and the resulting composition, that is, a seedfrom which a radicle has been produced before it is sown, is apregerminated seed.)

[0004] This is a most efficient and attractive way of seed treatment,but there remains the problem of the disposal of hazardous waste waterdespite efforts to minimize the concentration of the phytoprotectionproduct or the volume of the liquid. Another potential hazard of thisconventional seed soaking method is the generation of seeds that aretreated but unused for any reason. Said unused seeds can be hazardouswaste.

[0005] Rice seeds are commonly sown by dropping pregerminated seeds froman airplane over a flooded rice propagation area. Webster et al, in thepublication Hilgardia, 1973, vol. 41, pages 689-698, indicate thatsowing pregerminated rice seed in such a manner “introducescomplications not experienced with seed treatment in other cereals.”Further, the authors point out that the standard practice of soakingrice seed for 24 hours and then draining for 24 hours complicatesdevelopment of suitable methods of applying phytoprotection productssince “the protectant chemical must adhere to the seed in effectiveconcentrations throughout the soaking and planting process to beeffective during the initial period of seed germination and seedlingestablishment.” In an effort to arrive at a suitable method, Webster etal investigated the effects of several protectant chemicals, Difolatan,Captan and Thiram, applied before, after and during the soakingprocedure and measured effectiveness in terms of percent stand increaseover untreated control. They conclude that application prior to soakingafforded best total stand establishment. Application of phytochemicalafter soaking was found to give no increase in plant stand, that is, nosignificant protectant effect. No details as to the temperature orlength of soaking time or production of a radicle or size thereof weregiven. Moreover, the authors' recommendations to treat rice seed withphytoprotection products either before or during soaking, if used withthe preferred volumes of seeds according to the instant invention, wouldgenerate very large volumes of hazardous liquid waste.

[0006] International Patent Publication No. WO 93/01705 describes aprocess in which seed is coated by a foam and one or morephytoprotection products. According to the method described in thisdocument, there is simultaneously applied to plant seeds: (1) a liquidcomposition containing at least one phytoprotection product; and (2) afoam formed from a second composition containing at least onenon-phytotoxic foaming agent. The two compositions are broughtseparately into contact with the seeds while mixing to ensure ahomogeneous and even coating. WO 93/01705 states that “seeds thustreated may optionally be pregerminated.” The quoted expression isbelieved to clearly suggest optional pregermination of the seeds afterthe phytoprotection process and prior to planting (a step sequence whichWebster et al found most desirable). Further, the aforementioned problemof unused, treated seed is not obviated by the WO 93/01705 invention.

[0007] An object of the instant invention is to provide a highlyeffective method of preparing rice seeds for sowing.

[0008] Another object of the instant invention is to provide a highlyeffective method of preparing rice seeds for sowing, for example byplane.

[0009] Another object of the instant invention is to provide a processfor the preparation of rice seed for sowing in large quantities thatreduces or minimizes or even avoids altogether the generation ofhazardous, unusable seed.

[0010] Another object of the instant invention is to provide a processfor the preparation of rice seed for sowing that reduces or minimizes oreven avoids the problem of liquid waste.

[0011] Another object of the instant invention is to minimize theexposure of humans to phytoprotection products.

[0012] Another object of the instant invention is to provide a rapidmethod for the treatment of pregerminated rice seed by a phytoprotectionproduct.

[0013] Another object of the instant invention is to provide a method ofprotection of pregerminated rice seed against fungal pathogens.

[0014] Another object of the instant invention is to provide a method ofprotection of rice seed against insecticidal pests which is effectiveover a substantial period of time.

[0015] Another object of the instant invention is to provide a method ofprotection of rice seed which avoids the disadvantages of the knownmethods.

[0016] It has now been found that the above objects can be met in wholeor in part by the means of the instant invention. These and otherobjects will better appear during the description of the invention.

[0017] There is now provided a method of preparing rice seed for sowingcomprising the following steps:

[0018] (a) pregerminating said rice seed in water containingsubstantially no phytoprotection product at a temperature and during aperiod of time sufficient to produce a radicle having a size such thatthe said radicle is not substantially damaged in a subsequent seedtreatment process; and

[0019] (b) mixing the pregerminated seed thus obtained with an effectiveamount of a phytoprotection product.

[0020] A preferred embodiment of the invention is one in which theamount of said pregerminated seed is appropriate for sowing from theair, usually sowed in quantities between about 10 and about 20000 kg,more preferably between about 100 and about 1500 kg. The treatment ofsuch large quantities in such a short period of time and with minimumdamage to the grains is an especially difficult problem. Saidpregermination process is preferably contained in one or more bags. Bagsare water permeable containers that are optionally deformable,preferably able to contain between about 10 and about 1000 kg of seedbefore soaking. Sowing from the air generally entails the loading of anaircraft, preferably an airplane, followed by flying over the field tobe sown and distributing the seed to be sown. Another type of aircraftsuitable for sowing is a helicopter.

[0021] Another preferred embodiment of the invention is that the size ofthe radicle is between about 0.1 and about 15 mm, more preferablybetween about 1 and about 5 mm.

[0022] The mixing of said seed with the phytoprotection productgenerally takes place at or near (e.g., within about 50 kilometers of)an airport or airstrip, preferably within the legal boundaries of anairport used by said planes for sowing. Said mixing can optionally takeplace in a mixing apparatus that is in or on a truck, trailer, or othermovable device suitable for transporting said mixing apparatus. Inanother aspect of the invention, said seed to be pregerminated and mixedwith a phytoprotection product is transported by crane or forklift orhopper mechanism at each stage. Another mode of transportationcontemplated in the invention of said seed at each or any stage of themethod is by use of an auger.

[0023] By the term “phytoprotection product” is meant a material whichprovides an effective protection of rice seeds from pests' attacks. Theinvention is mainly directed to the protection of seeds and plantsderived from such seeds from insect attacks, particularly rice waterweevil, as well as from fungal attacks, in which cases thephytoprotection product comprises an insecticidally active compound orfungicidally active compound, respectively. The phytoprotection productswhich are used according to the present invention may also comprisessuch materials as biocontrol agents, that is, biological substances(typically, substances comprising fungi, bacteria or viruses) thatprotect seeds and plants derived from such seeds from insect and fungalattacks and/or provide nutrients to said seeds or plants derived fromsaid seeds. Another type of phytoprotection product contemplated by theinvention comprises the class of macronutrients and micronutrients, thatis, substances that function as a plant food. The phytoprotectionproduct may comprise more than one active ingredient, especially atleast one insecticide together with at least one fungicide. Also, one ormore biocontrol agents may be used together with one or moreinsecticides or one or more fungicides or both. One or moremacronutrients or micronutrients may also be used together with eachother and/or with one or more fungicides and/or insecticides and/orbiocontrol agents.

[0024] The phytoprotection product which is used to coat the rice seedis preferably a liquid composition, which may be aqueous or non-aqueous,in order to improve the speed of application. It may be fairly diversein nature and is defined in practice so as to be able to ensure thecoating upon the seed of the required effective amount of activematerial. It is preferably other than a gel. The preferred formulationsused in the invention can vary, for example, a solution, suspension,emulsion, or the like with a viscosity less than about 500 centipoises.The formulation used in the invention thus comprises, as necessaryconstituents, the active material and solvent, usually water; itoptionally and additionally contains other customary constituents usedin agrochemical formulations, for example those described inInternational Patent Publications No. WO 87/03781, 93/06089 and94/21606, as well as in European Patent Publication No. 0295117 and U.S.Pat. No. 5,232,940, all of which are incorporated by reference hereinand relied upon in their entireties, including their description ofagrochemical compositions and methods for formulating same. However,among the compositions described in this known art, it is preferable tochoose those which are more suited to rice seed coating. For example,sticking agents such as low molecular weight polymer often effectivelypromote sticking of the insecticidally active material upon the seed.The aqueous formulations used in the invention may also comprise anothernon-aqueous liquid phase.

[0025] The term “effective amount” as used herein means an amount of thephytoprotection product sufficient to produce the desired response; forexample, in the case of an insecticidal product, it is an insecticidallyeffective amount; in the case of a fungicidal product, it is afungicidally effective amount, etc.

[0026] According to a particularly preferred feature of the invention,the time from the end of pregermination period to the mixing of thepregerminated seed with the phytoprotection product is less than abouttwenty-four hours, preferably less than about eight hours. In anotheraspect of the invention, the time from the end of the pregerminationperiod to the sowing of the seed is less than about forty-eight hours,preferably less than about twenty-four hours and even more preferablyless than about eight hours.

[0027] In another aspect of the invention, the pregermination of riceseed is preferably provoked or activated during a period of timecomprised during about half a day to several days, preferably during aperiod comprised between one day and three days.

[0028] The following representative insecticidally active materials maybe used in accord with the present invention:

[0029] (E)-N¹-[(6-chloro-3-pyridyl)methyl]-N²-cyano-N¹-methylacetamidine(acetamiprid);

[0030] 1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamine(imidacloprid);

[0031] N-[(6-chloro-3-pyridinyl)methyl]-N-ethyl-N′-methyl-2-nitro-1,1-ethenediamine(nitenpyram);

[0032] [3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide(thiacloprid);

[0033]3-[(2-chloro-5-thiazolyl)methyl]tetrahydro-5-methyl-N-nitro-4H-1,3,5-oxadiazin-4-imine(CGA-293343);

[0034]1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazin-2(1H)-imine(AKD-1022);

[0035] N-methyl-N′-nitro-N″-[(tetrahydro-3-furanyl)methyl]-guanidine(MTI-446);

[0036] N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine(TI-435);

[0037] 2,3-dihydro-2,2-dimethylbenzofuran-7-yl methylcarbamate(carbofuran);

[0038] O,O-diethyl O-3,5,6-trichloro-2-pyridiyl phosphorothioate(chlorpyrifos);

[0039] 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea (diflubenzuron);

[0040] a pyrethroid such as (S)-α-cyano-3-phenoxybenzyl(S)-2-(4-chlorophenyl)-3-methylbutyrate (esfenvalerate);

[0041] [1α(S*),3α(Z)]-(±)-cyano(3-phenoxyphenyl)methyl3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate(lambda-cyhalothrin);

[0042] an insecticidal 1-aryl pyrazole;

[0043] an insecticidal 1-aryl pyrrole; or

[0044] an insecticidal 1-aryl imidazole.

[0045] The 1-arylpyrazoles which can be used according to the instantinvention are preferably compounds of formula (I):

[0046] wherein:

[0047] R₁ is CN or methyl;

[0048] R₂ is S(O)_(n)R₃;

[0049] R₃ is alkyl or haloalkyl;

[0050] R₄ represents a hydrogen or halogen atom or a member selectedfrom the group consisting of —NR₅R₆, —S(O)_(m)R₇, —C(O)R₇, —C(O)OR₇,alkyl, haloalkyl, —OR₈ and —N═C(R₉)(R₁₀);

[0051] R₅ and R₆ independently represent a hydrogen atom or an alkyl,haloalkyl, —C(O)alkyl, alkoxycarbonyl or —S(O)_(r)CF₃ radical; or R₅ andR₆ together form a divalent alkylene radical which can be interrupted byone or two divalent heteroatoms, such as oxygen or sulfur;

[0052] R₇ represents an alkyl or haloalkyl radical;

[0053] R₈ represents an alkyl or haloalkyl radical or a hydrogen atom;

[0054] R₉ represents an alkyl radical or a hydrogen atom;

[0055] R₁₀ represents a phenyl or heteroaryl group which isunsubstituted or substituted by one or more halogen atoms or a memberselected from the group consisting of OH, —O-alkyl, —S-alkyl, cyano andalkyl;

[0056] X represents a trivalent nitrogen atom or a C—R₁₂ radical, theother three valences of the carbon atom forming part of the aromaticring;

[0057] R₁₁ and R₁₂ represent, independently of each other, a hydrogen orhalogen atom;

[0058] R₁₃ represents a halogen atom or a haloalkyl, haloalkoxy,—S(O)_(q)CF₃ or —SF₅ group;

[0059] m, n, q and r represent, independently of one another, an integerequal to 0, 1 or 2;

[0060] provided that, when R₁ is methyl, then R₃ is haloalkyl, R₄ isNH₂, R₁₁ is Cl, R₁₃ is CF₃, and X is N.

[0061] The alkyl and alkoxy radicals and alkyl and alkoxy portions ofother radicals have one to six carbon atoms, preferably 1 to 4 carbonatoms, and can be branched or linear.

[0062] When R₅ and R₆ together form alkylene optionally interrupted byone or two hetero atoms, —NR₅R₆ preferably represents a 3- to 8-memberedring.

[0063] When R₁₀ is heteroaryl, it is preferably pyridyl, most preferably2-pyridyl.

[0064] A preferred group of effective 1-arylpyrazoles of formula (I) foruse in the present invention is that wherein:

[0065] R₁ is CN;

[0066] R₃ is a haloalkyl radical;

[0067] R₄ is NH₂;

[0068] X is C—R₁₂;

[0069] R₁₁ and R₁₂ represent, independently of one another, a halogenatom; and

[0070] R₁₃ is a haloalkyl radical.

[0071] A most preferred compound of formula (I) for use herein is5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinyl-3-cyanopyrazole,also known as5-amino-1-(2-6-dichloro-α,α,α-trifluoro-p-tolyl)-4-trifluoromethyl-sulfinylpyrazole-3-carbonitrileor fipronil and hereafter designated as Compound A.

[0072] Compounds of formula (I) may be prepared according to knownprocesses, for example as described in International Patent PublicationsNo. WO 87/03781, 93/06089, and 94/21606 as well as in European PatentPublications No. 0295117, 0403300, 0385809 and 0679650, German PatentPublication No. 19511269 and U.S. Pat. Nos. 5,232,940 and 5,236,938 (allof which are incorporated by reference herein and relied upon in theirentireties, especially for their description of compounds of formula (I)and methods for their preparation and use, both general and specific),or other process according to the knowledge of a man skilled in the artof chemical synthesis.

[0073] Representative fungicides that may be used in the method of theinvention include the following:

[0074] [[1,2-ethanediylbis[carbamodithioato]](2-)]manganese mixture with[[1,2-ethanediylbis [carbamodithioato]](2—)]zinc (mancozeb);

[0075] methyl 1-(butylcarbamoyl)benzimidazol-2-ylcarbamate (benomyl);

[0076] 3-(3,5-dichlorophenyl)-N-(1-isopropyl)-2,4-dioxoimidazolidine-1-carboxamide (iprodione);

[0077] ethyl hydrogen phosphonate (fosetyl);

[0078] ethyl hydrogen phosphonate aluminum salt (fosetyl-aluminum);

[0079] tetramethylthiuram disulfide (thiram);

[0080](±)-1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl-1H-1,2,4-triazole(propiconazole);

[0081](±)-E-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol(triticonazole);

[0082] 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxanilide (carboxin);

[0083] methyl N-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate(metalaxyl);

[0084] methyl(E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate(azoxystrobin); or

[0085] a copper fungicide, such as but not limited to dicopper chloridetrihydroxide.

[0086] Representative biocontrol agents that may be used in the methodof the invention include:

[0087]Bacillus thuringiensis;

[0088]Bacillus subtilis;

[0089] Pseudomonas spp.;

[0090] Rhizobium spp.;

[0091] Azospirillum spp.; or

[0092] Beauveria spp.

[0093] Micronutrients and macronutrients that may be used according tothe invention include:

[0094] iron chelates;

[0095] zinc chelates;

[0096] manganese chelates; or

[0097] nitrogen.

[0098] As noted above, in another aspect of the invention,phytoprotection products may be mixed with the above seed separately,together or in any combination as specified in standard referencematerial for those skilled in the art of the application ofphytoprotection products.

[0099] The amount of phytoprotection product, preferably aninsecticidally active material, may depend very much on the particularproduct being used. Generally the amount of active ingredient which isapplied to the pregerminated seed is between about 2 and about 1000 g/q(gram of active ingredient per quintal of germinated seed), preferably(especially for the 1-aryl pyrazoles or imidacloprid) between about 5and about 800 g/q, still more preferably between about 5 and about 100g/q.

[0100] In yet another aspect, the present invention relates to a newprocess for cultivating rice and new improved rice seed.

[0101] It is known to improve rice seed by treating such seed by meansof plant growth regulators such as gibberellic acid so as to getstronger and better plants, better and stronger germination and thusobtain better growing and cropping conditions. Furthermore, planted riceseed or the rice crops therefrom are also attacked by a number of pestsor can suffer predation by birds. Another problem associated with ricecropping is the displacement of said rice plants upon flooding ricefields, a common agricultural practice. Current methods for protectingrice and rice seed are already discussed hereinabove.

[0102] In accord with this further aspect of the present invention, oneobject is to still further improve the rice seed, rice germination, riceplant, rice plant growing and rice plant cropping.

[0103] Another object of this further aspect of the instant invention isto provide an improved method of rice cultivation.

[0104] Another object of this further aspect of the instant invention isto provide a method of having stronger rice seedlings or plants whichhave a better resistance to wind and rain.

[0105] Another object of this further aspect of the instant invention isto provide an improved process for the preparation of rice seed forsowing.

[0106] Another object of this further aspect of the instant invention isto provide a new seed which is designed for sowing by plane.

[0107] Another object of this further aspect of the instant invention isto provide a highly effective method of preparing rice seeds for sowingby plane.

[0108] Another object of this further aspect of the instant invention isto provide a process for the preparation of rice seed for sowing inlarge quantities that reduces or minimizes or even avoids altogether thegeneration of hazardous, unusable seed.

[0109] Another object of this further aspect of the instant invention isto provide a process for the preparation of rice seed for sowing thatreduces or minimizes or even avoids the problem of liquid waste.

[0110] Another object of this further aspect of the instant invention isto minimize the exposure of humans to phytoprotection products.

[0111] Another object of this further aspect of the instant invention isto provide a rapid method for the treatment of rice seed by aphytoprotection product.

[0112] Another object of this further aspect of the instant invention isto provide a method of protection of rice seed against insect pestswhich is effective over a substantial period of time.

[0113] Another object of this further aspect of the instant invention isto provide a method of protection of rice seed which avoids thedisadvantages of the known methods.

[0114] These and other objects will better appear during the descriptionof this further aspect of the invention. It has now been found thatthese objects can be met in whole or in part by means of this furtheraspect of the instant invention.

[0115] A first embodiment of this further aspect of the instantinvention is a new seed which is a pregerminated rice seed comprising(preferably as a coating) a plant growth regulator, preferably agibberellin, more preferably gibberellic acid.

[0116] Another embodiment of this further aspect of the invention isrelated to pregerminated rice seed comprising a plant growth regulator(preferably a gibberellin, more preferably gibberellic acid), said seedhaving a radicle size such that said radicle is not substantiallydamaged by the seed treatment process. Practically speaking, said seedgenerally has a radicle size from about 0.1 to about 15 mm, preferablyfrom about 0.5 to about 10 mm, even more preferably from about 1 toabout 5 mm.

[0117] There is also provided by this further aspect of the presentinvention a method of preparation of rice seed for sowing comprising thefollowing steps:

[0118] (a) pregerminating said rice seed in water containingsubstantially no phytoprotection product or plant growth regulator at atemperature and during a period of time sufficient to produce a radiclehaving a size such that said radicle is not substantially damaged in asubsequent seed treatment process; and

[0119] (b) mixing the pregerminated seed thus obtained with an effectiveamount of plant growth regulator (preferably a gibberellin, morepreferably gibberellic acid).

[0120] A preferred embodiment of this further aspect of the invention isone in which the amount of said pregerminated seed is appropriate forsowing from the air, usually sowed in quantities between about 10 andabout 20000 kg, more preferably between about 100 and about 1500 kg. Thetreatment of such large quantities in such a short period of time andwith minimum damage to the grains is an especially difficult problem.

[0121] Said pregermination process is preferably contained in one ormore bags. Bags are water permeable containers that are optionallydeformable, preferably able to contain between about 10 and about 1000kg of seed before soaking. Sowing from the air generally entails theloading of an aircraft, preferably an airplane, followed by flying overthe field to be sown and distributing the seed to be sown. Another typeof aircraft suitable for sowing is a helicopter.

[0122] The plant growth regulator which can be used in this furtheraspect of the instant invention is preferably used as a compositioncomprising an effective amount of plant growth regulator, preferably agibberellin, more preferably gibberellic acid, which optionally furthercomprises one or more phytoprotection products.

[0123] The plant growth regulator can be used in this further aspect ofthe present invention together with a phytoprotection product as definedhereinafter.

[0124] The seed as hereinabove described is usually brought into contactwith the plant growth regulator by mixing. The mixing of said seed witha plant growth regulator generally takes place at or near (e.g., withinabout 50 kilometers of) an airport or airstrip, preferably within thelegal boundaries of an airport used by said planes for sowing. Saidmixing can optionally take place in a mixing apparatus that is in or ona truck, trailer, or other movable device suitable for transporting saidmixing apparatus. In another embodiment of this further aspect of theinvention, said seed to be pregerminated and mixed with a plant growthregulator is transported by crane or forklift or hopper mechanism ateach stage. Another contemplated mode of transportation of the seed ateach or any stage of the method of this further aspect of the inventionis by use of an auger.

[0125] The plant growth regulator which is used to coat the rice seed ispreferably a liquid composition, which may be aqueous or non-aqueous, inorder to improve the speed of application. It may be fairly diverse innature and is defined in practice so as to be able to ensure the coatingupon the seed of the required effective amount of active material. It ispreferably other than a gel. The formulation used in this further aspectof the invention can be, for example, a solution, suspension, emulsion,suspoemulsion (that is to say, an emulsion which is simultaneously asuspension), powder dissolved or suspended in liquid, or the like. Theviscosity of this liquid composition is preferably less than about 500centipoises. The formulation used in this further aspect of theinvention thus comprises, as necessary constituents, the activematerial(s) and solvent(s), usually water; it optionally andadditionally contains other customary constituents used in agrochemicalformulations, for example those described in International PatentPublications No. WO 87/03781, 93/06089 and 94/21606 as well as inEuropean Patent Publication No. 0295117 and U.S. Pat. No. 5,232,940, allof which are incorporated by reference herein and relied upon in theirentireties for their description of agrochemical compositions andmethods for formulating same.

[0126] Among the compositions which can be used in this further aspectof the invention, it is preferable to choose those which are more suitedto rice seed coating. For example, sticking agents such as low molecularweight polymer, e.g. latex polymer formulations, often effectivelypromote sticking of the plant growth regulating material orphytoprotection product upon the seed. The aqueous formulations used inthis further aspect of the invention may also comprise anothernon-aqueous liquid phase.

[0127] The term “phytoprotection product” used in connection with thisfurther aspect of the invention has the same meaning as usedhereinabove. The phytoprotection products which are particularlypreferred for use with this further aspect of the invention are likewisethose already described hereinabove, especially insecticides andfungicides, and also biocontrol agents and macronutrients andmicronutrients as previously defined herein.

[0128] By the term “plant growth regulator” is meant any substance orproduct or composition or compound that promotes plant or root growth,or both, as understood by those skilled in the art of plant growthregulating effects. The known effects of gibberellic acid are typical ofplant growth regulating effects as meant in the present specification.

[0129] The term “effective amount” as used herein means an amount of theplant growth regulator or phytoprotection product sufficient to producethe desired response; for example, in the case of the plant growthregulator, an effective plant growth regulating amount; in the case ofan insecticide, an insecticidally effective amount; in the case of afungicide, a fungicidally effective amount, etc.

[0130] According to a particularly preferred feature of this furtheraspect of the invention, the time from the end of the pregerminationperiod to the mixing of the pregerminated seed with the plant growthregulator is less than about twenty-four hours, preferably less thanabout eight hours. In another feature of this further aspect of theinvention, the time from the end of the pregermination period to thesowing of the seed is less than about forty-eight hours, preferably lessthan about twenty-four hours, even more preferably less than about eighthours.

[0131] In another aspect of this further aspect of the invention, thepregermination of rice seed is preferably provoked or activated during aperiod of time from about half a day to five days, preferably during aperiod comprised from one day to three days.

[0132] According to another and important feature of this further aspectof the invention, the seed is treated with a plant growth regulatorcomprising gibberellic acid and an insecticidally active ingredient,wherein the ratio of the insecticidally active ingredient to gibberellicacid depends upon the specific insecticidally active ingredient which isused. This ratio (insecticidally active ingredient / gibberellin; w/w)is generally comprised in a range from about 10/1 to about 1000/1,preferably from about 20/1 to about 200/1.

[0133] In a particularly preferred embodiment of this further aspect ofthe invention, the insecticidally active ingredient is selected from thegroup comprising all of the representative insecticidally activematerials named hereinabove.

[0134] The insecticidal 1-arylpyrazoles which can be used according tothis further aspect of the instant invention are preferably compounds offormula (I):

[0135] in which:

[0136] R₁ is CN or methyl;

[0137] R₂ is S(O)_(n)R₃;

[0138] R₃ is alkyl or haloalkyl;

[0139] R₄ represents a hydrogen or halogen atom or a member selectedfrom the group consisting of NR₅R₆, S(O)_(m)R₇, C(O)R₇, C(O)O—R₇, alkyl,haloalkyl, OR₈ and

[0140] —N═C(R₉)(R₁₀);

[0141] R₅ and R₆ independently represent a hydrogen atom or an alkyl,haloalkyl, C(O)alkyl, alkoxycarbonyl or S(O)_(r)CF₃ radical; or R₅ andR₆ together form a divalent alkylene radical which is optionallyinterrupted by one or two heteroatoms, such as oxygen, nitrogen orsulfur;

[0142] R₇ represents an alkyl or haloalkyl radical;

[0143] R₈ represents an alkyl or haloalkyl radical or a hydrogen atom;

[0144] R₉ represents an alkyl radical or a hydrogen atom;

[0145] R₁₀ represents a phenyl or heteroaryl group which isunsubstituted or substituted by one or more halogen, OH, —O-alkyl,—S-alkyl, cyano, or alkyl;

[0146] X represents a trivalent nitrogen atom or a C—R₁₂ radical, theother three valences of the carbon atom forming part of the aromaticring;

[0147] R₁₁ and R₁₂ represent, independently of each other, a hydrogen orhalogen atom;

[0148] R₁₃ represents a halogen atom or a haloalkyl, haloalkoxy,S(O)_(q)CF₃ or SF₅ group; and

[0149] m, n, q, and r represent, independently of one another, aninteger equal to 0, 1, or 2;

[0150] provided that, when R₁ is methyl, then R₃ is haloalkyl, R₄ isNH₂, R₁₁ is Cl, R₁₃ is CF₃ and X is N.

[0151] The alkyl and alkoxy radicals and alkyl and alkoxy portions ofother radicals have one to six carbon atoms and can be branched orlinear. The haloalkyl and haloalkoxy groups preferably have one to fourcarbon atoms. The haloalkyl and haloalkoxy groups can bear one or morehalogen atoms; preferred groups of this type include —CF₃ and —OCF₃.

[0152] When R₅ and R₆ together form alkylene optionally interrupted byone or two hetero atoms, —NR₅R₆ preferably represents a 3 to 8-memberedring, most preferably a 5, 6 or 7-membered ring.

[0153] When R₁₀ is heteroaryl, it is preferably pyridyl, most preferably2-pyridyl.

[0154] It will be understood that the 1-arylpyrazoles of formula (I)include enantiomers and/or diastereomers thereof.

[0155] A preferred group of 1-arylpyrazoles for use in this furtheraspect of the present invention comprises compounds of formula (I) withone or more of the following features:

[0156] R₁ is CN;

[0157] R₄ is —NR₅R₆;

[0158] R₅ and R₆ are independently selected from hydrogen, alkyl,haloalkyl, C(O)alkyl or alkoxycarbonyl;

[0159] X is C—R₁₂;

[0160] R₁₃ is halogen, haloalkyl, haloalkoxy or —SF₅.

[0161] Another preferred group of effective 1-arylpyrazoles of formula(I) for use in this further aspect of the present invention is thatwherein:

[0162] R₁ is CN;

[0163] R₃ is a haloalkyl radical;

[0164] R₄ is NH₂;

[0165] X is C—R₁₂;

[0166] R₁₁ and R₁₂ represent, independently of each other, a halogenatom; and

[0167] R₁₃ is a haloalkyl radical.

[0168] A most preferred compound of formula (I) for use herein in thisfurther aspect of the invention is5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinyl-3-cyanopyrazole,also known as fipronil and hereafter designated as Compound A.

[0169] Compounds of formula (I) may be prepared according to knownprocesses, for example as described in International Patent PublicationsNo. WO 87/03781, 93/06089, and 94/21606 as well as in European PatentPublications No. 0295117, 0403300, 0385809 and 0679650, German PatentPublication No. 19511269 and U.S. Pat. Nos. 5,232,940 and 5,236,938 (allof which are already incorporated by reference hereinabove and reliedupon in their entireties, especially for their description of compoundsof formula (I) and methods for their preparation and use, both generaland specific), or other process according to the knowledge of a manskilled in the art of chemical synthesis.

[0170] Representative fungicides that may be used in the method of thisfurther aspect of the invention include all of the representativefungicides named hereinabove.

[0171] Similarly, representative biocontrol agents, micronutrients andmacronutrients that may be used in the method of this further aspect ofthe invention include all those named earlier in this description.

[0172] The gibberellins are a known group of plant growth regulatorswhich has been described in inter alia, The Pesticide Manual, 10thedition, (1994), The British Crop Protection Council, London.Gibberellic acid is a member of this group.

[0173] In another embodiment of this further aspect of the invention,phytoprotection products may be mixed with the seed separately, togetheror in any combination as specified in standard reference material forthose skilled in the art of the application of phytoprotection products,in addition of course to the plant growth regulator.

[0174] The amount of pesticidally active, preferably insecticidallyactive, material may depend very much of the particular pesticide orinsecticide being used in this further aspect of the present invention.Generally, the amount of active ingredient which is applied to thepregerminated seed is comprised between about 2 and about 1000 g/q.(gram of active ingredient per quintal of germinated seed), preferably(especially for the 1-aryl pyrazoles or imidacloprid) between about 5and about 800 g/q., still more preferably between about 5 and about 100g/q.

[0175] According to a further embodiment of this further aspect of theinvention, there is now provided a new composition of matter which is adry pregerminated seed rice comprising on its surface a plant growthregulating agent, preferably a gibberellin, and more preferablygibberellic acid, and optionally a pesticidally active ingredient suchan insecticidally active ingredient. The dry seed may be dry only at theoutside part of the seed; some humidity may be present in the inner partof the seed. This dry germinated seed has a radicle whose size isgenerally between about 0.1 mm up to about 15 mm, preferably betweenabout 0.5 and about 10 mm.

[0176] The amount of plant growth regulating agent, preferably ofgibberellic acid, laid upon the seed in this further aspect of theinvention is generally comprised between about 0.01 and about 50 g/q.(gram of active ingredient per quintal of pregerminated seed),preferably (especially for gibberellic acid) between about 0.1 and about5 g/q., still more preferably between about 0.3 and about 3 g/q.

[0177] The amount of pesticidally active ingredient, preferably ofinsecticidally active ingredient, laid upon the seed in this furtheraspect of the invention is generally comprised between about 2 and about1000 g/q. (gram of active ingredient per quintal of germinated seed),preferably (especially for the 1-aryl pyrazoles or imidacloprid) betweenabout 5 and about 800 g/q., still more preferably between about 5 andabout 100 g/q.

[0178] In the various methods or processes for treating rice seeds asdefined above in accord with this further aspect of the invention, theamount of formulation brought directly into contact with the seed (orpropagation material) to be treated is generally between about 0.1% andabout 20%, preferably between about 0.5% and about 1.5%, of the weightof seeds to be treated. Values outside these ranges, whether more orless, can also be used but without substantial or specific advantage.

[0179] This further aspect of the invention also relates to a processfor cultivating and/or growing rice in which the germinated rice seed,as hereinabove defined, coated or otherwise combined with a compositioncomprising an effective dose of plant growth regulating agent, andoptionally of pesticidally active ingredient, is sown. The process issuch that, for a long subsequent period after germination, preferablyfor the rest of the growing season, it does not comprise any othertreatment (either of the seed or of the plant resulting therefrom) toprotect the plants against the same insects (that is to say, no otherinsecticidal treatment). This means that the effectiveness of theprocess according to the instant invention is often sufficient toeliminate the need for another insecticide treatment altogether.

[0180] This further aspect of the invention also relates to a mass, orcollection, of germinated (or, in other words, pre-germinated) riceseeds, in which the seeds are in the form of grains which have alreadygerminated (in other words, these seeds have already their firstradicle), and are at the same time covered or coated (e.g. bathed in orsprayed on) with a formulation as defined above and containing a plantgrowth regulating agent, and optionally a phytoprotection product(preferably an insecticide) as herein described, especially those offormula (I).

[0181] The improved seeds of this further aspect of the invention, whengerminated and grown, have a bigger shoot and a bigger root thanuntreated seeds. Known rice seeds treated by gibberellic acid usuallyhad a bigger shoot, but not a bigger root than the untreated seed.According to a feature of this further aspect of the invention, theseeds are such that the radicle and the shoot are generally the samelength. Furthermore, the improved seeds of this further aspect of theinvention are more resistant to being uprooted or displaced by windafter sowing, especially 2 or 3 days or more after sowing. Thisadvantage exists even if the seed is not in a deep location in the soil.Another advantage to this method is that said seeds are less likely tobe eaten by birds since a sown rice field can be quickly flooded toprevent such eating. Another advantage of this aspect of the instantinvention is that, since the rice plants resulting from the said seedtreatment are more quickly and firmly established, herbicides can beapplied earlier before any weeds become large, thus contributing to theefficacy of the herbicides.

[0182] In another important embodiment of this further aspect of theinvention, there is now provided a composition comprising a plant growthregulator and a phytoprotection product which is an insecticidal1-arylpyrazole, an insecticidal 1-arylpyrrole or an insecticidal1-arylimidazole, preferably an insecticidal 1-arylpyrazole of formula(I):

[0183] wherein:

[0184] R₁ is CN or methyl;

[0185] R₂ is S(O)_(n)R₃;

[0186] R₃ is alkyl or haloalkyl;

[0187] R₄ is hydrogen, halogen, —NR₅R₆, —C(O)OR₇, -S(O)_(m)R₇, alkyl,haloalkyl, —OR₈, —N═C(R₉)(R₁₀) or C(O)R₇;

[0188] R₅ and R₆ independently represent hydrogen, alkyl, haloalkyl,—C(O)alkyl, alkoxycarbonyl or —S(O)_(r)CF₃; or R₅ and R₆ form together adivalent alkylene radical which is optionally interrupted by one or moreheteroatoms, preferably selected from the group consisting of oxygen,nitrogen and sulfur;

[0189] R₇ is alkyl or haloalkyl;

[0190] R₈ is alkyl, haloalkyl or hydrogen;

[0191] R₉ is hydrogen or alkyl;

[0192] R₁₀ is a phenyl or heteroaryl group, each of which isunsubstituted or substituted by one or more hydroxy, halogen, —O-alkyl,—S-alkyl, cyano, or alkyl or combinations thereof;

[0193] X is nitrogen or —C—R₁₂;

[0194] R₁₁ and R₁₂ are independently halogen or hydrogen;

[0195] R₁₃ is halogen, haloalkyl, haloalkoxy, —S(O)_(q)CF₃ or —SF₅; and

[0196] m, n, q and r are independently selected from 0, 1, and 2;

[0197] provided that when R₁ is methyl, then R₃ is haloalkyl, R₄ is NH₂,R₁₁ is Cl, R₁₃ is CF₃, and X is N.

[0198] Even more preferably in the composition described immediatelyabove, the plant growth regulator is a gibberellin, preferablygibberellic acid, and the insecticidal 1-arylpyrazole is5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinyl-3-cyanopyrazole.

[0199] The following examples are descriptive, and are not to be takenas limiting examples. Other choices of materials, methods, and organismswill be obvious to those skilled in the art in light of the teachingherein.

EXAMPLE 1

[0200] Rice seeds (227 kg) were soaked at 25°C. in water for 24 hours.The seeds were removed from water and allowed to drain for 30 hours. Theseeds were drained completely, allowed to absorb excess water, and wereallowed to germinate up to the point of having emerging radicles whosesize was between 1 and 8 mm.

[0201] These seeds were treated by thorough machine mixing with a latexpolymer formulation containing about 3% of fipronil. The thus-obtainedpregerminated seeds appeared undamaged and had a normal coating offipronil.

[0202] Seed was tested for germination in an incubator and also flownonto a flooded field under standard agricultural practices. The treatedseeds behaved the same as untreated seeds, i.e., stand establishment wasthe same as untreated seed.

EXAMPLE 2

[0203] One thousand pounds of rice seeds (450 kg) were pregerminated inone bag by soaking the bag in water for twenty-four hours followed bydraining for twenty-four hours. The seeds were treated immediately withmancozeb in a slurry at a rate of 19-22 fluid ounces (570-630 mL) perhundred pounds (45 kg) of seed. The seed was flown onto flooded fieldswhere it established an acceptable stand of rice plants.

EXAMPLE 3

[0204] Rice seeds (227 kg) were soaked at 25°C. in water for 24 hours.The seed was removed from water and allowed to drain for 30 hours. Theseeds were allowed to absorb excess water, and were allowed to germinateup to the point of having emerging radicles whose size was between 1 and8 mm.

[0205] These seeds were treated by thorough machine mixing with a latexpolymer formulation containing about 0.2% w/v of gibberellic acid. Thethus-obtained germinated seeds appeared undamaged and had a coatingcomprising gibberellic acid.

[0206] Seed was sown by plane in a flooded field. After a period of timeof 3 to 10 days, it was observed that the shoots had about the same sizeas the shoots obtained with classical treatment of rice seed withgibberellic acid; however, the root and the shoot were of approximatelythe same size, contrary to the size obtained with classical treatment ofrice seed with gibberellic acid (in which the root is smaller); theseedlings were highly resistant to wind even though they were located inthe soil at a depth as small as 0 to 2 mm (less deep than that formedwith classical treatment of rice seed with gibberellic acid).

EXAMPLE 4

[0207] The procedure of Example 3 was repeated except that thepregerminated seeds were coated with the same treatment of gibberellicacid as in Example 3 and with mancozeb in a slurry at a rate of 19-22fluid ounces (570-630 mL) per hundred pounds (45 kg) of seed.

[0208] Seeds were then sown by plane onto a flooded field where the sameobservations were made as in Example 3.

EXAMPLE 5

[0209] The procedure of Example 3 is repeated, except that the latexpolymer formulation containing about 0.2% w/v gibberellic acid furthercontains about 3% w/v of Compound A. Seeds are then sown by plane onto aflooded field.

[0210] While the invention has been described in terms of variouspreferred embodiments, the skilled artisan will appreciate that variousmodifications, substitutions, omissions and changes may be made withoutdeparting from the spirit thereof. Accordingly, it is intended that thescope of the present invention be limited solely by the scope of thefollowing claims, including equivalents thereof.

What is claimed is:
 1. A method of preparation of rice seed for sowingcomprising the following steps: (a) pregerminating said rice seed inwater containing substantially no phytoprotection product or plantgrowth regulator at a temperature and for a period of time sufficient toproduce a radicle having a size of from about 0.1 to about 15 mm; and(b) mixing the pregerminated seed thus obtained with an effective amountof plant growth regulator.
 2. A method according to claim 1 , whereinthe plant growth regulator is a gibberellin.
 3. A method according toclaim 2 , wherein the gibberellin is gibberellic acid.
 4. A methodaccording to claim 1 , wherein the amount of said pregerminated seed forsowing is between about 10 and about 20000 kg.
 5. A method according toclaim 4 , wherein the amount of said pregerminated seed for sowing isbetween about 100 and about 1500 kg.
 6. A method according to claim 1 ,wherein the amount of said pregerminated seed is contained in one ormore bags.
 7. A method according to claim 1 , wherein said pregerminatedseed is prepared near or at an airport or airstrip.
 8. A methodaccording to claim 1 , wherein said pregerminated seed is treated instep (b) by mixing with a liquid composition comprising the plant growthregulator.
 9. A method according to claim 8 , wherein said liquidcomposition is an aqueous liquid.
 10. A method according to claim 9 ,wherein said aqueous liquid has a viscosity of less than 500centipoises.
 11. A method according to claim 1 , wherein saidpregerminated seed is treated in step (b) by mixing with a compositioncomprising the plant growth regulator and a phytoprotection product. 12.A method according to claim 1 , wherein the time from the end ofpregermination period to the mixing of the pregerminated seed with theplant growth regulator is less than twenty-four hours.
 13. A methodaccording to claim 12 , wherein the time from the end of thepregermination period to the mixing of the pregerminated seed with theplant growth regulator is less than eight hours.
 14. A method accordingto claim 1 , wherein the time from the end of pregermination period tothe sowing of the seed is less than forty-eight hours.
 15. A methodaccording to claim 14 , wherein the time from the end of thepregermination period to the sowing of the seed is less than twenty-fourhours.
 16. A method according to claim 15 , wherein the time from theend of the pregermination period to the sowing of the seed is less thaneight hours.
 17. A method according to claim 11 , wherein thephytoprotection product is an insecticidally active ingredient.
 18. Amethod according to claim 17 , wherein the plant growth regulator is agibberellin.
 19. A method according to claim 18 , wherein thegibberellin is gibberellic acid.
 20. A method according to claim 19 ,wherein the weight/weight ratio of the insecticidally active ingredientto gibberellic acid is from about 10/1 to about 1000/1.
 21. A methodaccording to claim 20 , wherein the weight/weight ratio of theinsecticidally active ingredient to gibberellic acid is from about 20/1to about 200/1.
 22. A method according to claim 11 , wherein thephytoprotection product is selected from the group consisting ofacetamiprid, imidacloprid, carbofuran, chlorpyrifos, diflubenzuron,esfenvalerate, lambda-cyhalothrin, an insecticidal 1-aryl pyrazole, aninsecticidal 1-aryl pyrrole, an insecticidal 1-aryl imidazole, mancozeb,benomyl, iprodione, fosetyl, fosetyl-aluminum, thiram, propiconazole,triticonazole, carboxin, metalaxyl, azoxystrobin, a copper fungicide,Bacillus thuringiensis, Bacillus subtilis, Pseudomonas spp., Rhizobiumspp., Azospirillum spp., Beauveria spp., an iron chelate, a zinc chelateand a manganese chelate.
 23. A method according to claim 11 , whereinthe phytoprotection product is:N-[(6-chloro-3-pyridinyl)methyl]-N-ethyl-N′-methyl-2-nitro-1,1-ethenediamine(nitenpyram);[3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide(thiacloprid);3-[(2-chloro-5-thiazolyl)methyl]tetrahydro-5-methyl-N-nitro-4H-1,3,5-oxadiazin-4-imine(CGA-293343);1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazin-2(1H)-imine(AKD-1022);N-methyl-N′-nitro-N″-[(tetrahydro-3-furanyl)methyl]-guanidine (MTI-446);or N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine(TI-435).
 24. A method according to claim 22 , wherein the insecticidal1-arylpyrazole is a compound of the formula:

in which: R₁ is CN or methyl; R₂ is S(O)_(n)R₃; R₃ is alkyl orhaloalkyl; R₄ represents a hydrogen or halogen atom or a member selectedfrom the group consisting of NR₅R₆, S(O)_(m)R₇, C(O)R₇, C(O)O—R₇, alkyl,haloalkyl, OR₈ and —N═C(R₉)(R₁₀); R₅ and R₆ independently represent ahydrogen atom or an alkyl, haloalkyl, C(O)alkyl, alkoxycarbonyl orS(O)_(r)CF₃ radical; or R₅ and R₆ together form a divalent alkyleneradical which is optionally interrupted by one or two heteroatoms; R₇represents an alkyl or haloalkyl radical; R₈ represents an alkyl orhaloalkyl radical or a hydrogen atom; R₉ represents an alkyl radical ora hydrogen atom; R₁₀ represents a phenyl or heteroaryl group which isunsubstituted or substituted by one or more halogen, OH, —O-alkyl,—S-alkyl, cyano, or alkyl; X represents a trivalent nitrogen atom or aC—R₁₂ radical, the other three valences of the carbon atom forming partof the aromatic ring; R₁₁ and R₁₂ represent, independently of eachother, a hydrogen or halogen atom; R₁₃ represents a halogen atom or ahaloalkyl, haloalkoxy, S(O)_(q)CF₃ or SF₅ group; and m, n, q, and rrepresent, independently of one another, an integer equal to 0, 1, or 2;provided that, when R₁ is methyl, then R₃ is haloalkyl, R₄ is NH₂, R₁₁is Cl, R₁₃ is CF₃ and X is N.
 25. A method according to claim 24 ,wherein, in the compound of formula (I), R₁ is CN; R₃ is a haloalkylradical; R₄ is NH₂; X is C—R₁₂; R₁₁ and R₁₂ represent, independently ofeach other, a halogen atom; and R₁₃ is a haloalkyl radical.
 26. A methodaccording to claim 25 , wherein the compound of formula (I) is5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinyl-3-cyanopyrazole.27. A method according to claim 26 , wherein the plant growth regulatoris a gibberellin.
 28. A method according to claim 27 , wherein thegibberellin is gibberellic acid.
 29. A method according to claim 28 ,wherein the weight/weight ratio of5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinyl-3-cyanopyrazoleto gibberellic acid is from about 10/1 to about 1000/1.
 30. A methodaccording to claim 29 , wherein the weight/weight ratio of5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinyl-3-cyanopyrazoleto gibberellic acid is from about 20/1 to about 200/1.
 31. A methodaccording to claim 11 , wherein the phytoprotection product is apesticidally active ingredient which is applied to the pregerminatedseed in an amount of between about 2 and about 1000 g/q.
 32. A methodaccording to claim 31 , wherein the amount of pesticidally activeingredient applied is between about 5 and about 800 g/q.
 33. A methodaccording to claim 32 , wherein the pesticidally active ingredient is a1-aryl pyrazole or imidacloprid.
 34. A method according to claim 32 ,wherein the amount of pesticidally active ingredient applied is betweenabout 5 and about 100 g/q.
 35. A method according to claim 1 , whereinthe size of the radicle of the seed is from about 0.5 mm to about 10 mm.36. A method according to claim 1 , wherein the amount of plant growthregulator laid upon the seed is from about 0.01 to about 50 g/q.
 37. Amethod according to claim 36 , wherein the amount of the plant growthregulator laid upon the seed is from about 0.1 to about 5 g/q.
 38. Amethod according to claim 37 , wherein the amount of the plant growthregulator laid upon the seed is from about 0.3 to about 3 g/q.
 39. Amethod according to claim 17 , wherein, for a long period of timesubsequent to germination, no further treatment of the seed or of theplant resulting therefrom is used to protect the plant against the sameinsects.
 40. A method according to claim 39 , wherein, for the remainderof the growing season, no further treatment of the seed or of the plantresulting therefrom is used to protect the plant against the sameinsects.